WO1992022629A1 - Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol - Google Patents

Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol Download PDF

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Publication number
WO1992022629A1
WO1992022629A1 PCT/US1992/004902 US9204902W WO9222629A1 WO 1992022629 A1 WO1992022629 A1 WO 1992022629A1 US 9204902 W US9204902 W US 9204902W WO 9222629 A1 WO9222629 A1 WO 9222629A1
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Prior art keywords
alkyl
laundry detergent
weight
surfactants
composition according
Prior art date
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PCT/US1992/004902
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English (en)
French (fr)
Inventor
Gerard Marcel Baillely
Suzanne Powell
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The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP5501005A priority Critical patent/JPH06508394A/ja
Priority to AU22482/92A priority patent/AU667047B2/en
Priority to DE69222418T priority patent/DE69222418T2/de
Priority to BR9206176A priority patent/BR9206176A/pt
Priority to EP92914366A priority patent/EP0591397B1/en
Publication of WO1992022629A1 publication Critical patent/WO1992022629A1/en
Priority to GR970402296T priority patent/GR3024776T3/el

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • nonionic surfactant is commonly used to obtain an acceptable balance of particulate soil removal and grease and oily soil removal characteristics.
  • Detergent compositions incorporating surfactant systems in which the major component is nonionic are known in the art, e.g. EP-A-0006268 and GB 2206601 but any commercial application has tended to be of a specialist nature. This is because compositions based on anionic surfactants provide acceptable detergency over a broader spectrum of soil types, display greater compatibility with adjuncts such as optical brighteners and fabric softening additives and are also less aggressive towards fabric dyestuffs and washing machine components.
  • N-methyl, coconut fatty acid glucamide N-methyl, coconut fatty acid glucamide.
  • the thickening properties of the amides are indicated as being of particular use in liquid surfactant systems containing paraffin sulfonate, although the aqueous surfactant systems can contain other anionic surfactants, such as alkylaryl sulfonates, olefin sulfonate, sulfosuccinic acid half ester salts, and fatty alcohol ether sulfonates, and nonionic surfactants such as fatty alcohol polyglycol ether, alkylphenol polyglycol ether, fatty acid polyglycol ester, polypropylene oxlde-polyethylent oxide mixed polymers, etc.
  • glucamide surfactants are disclosed, for example, in DT 2,226,872, published December 20, 1973, H. W. Eckert, et al., which relates to washing compositions comprising one or more surfactants and builder salts selected from polymeric phosphates, sequestering agents, and washing alkalis, Improved by the addition of an N-acylpolyhydroxyalkyl-amine of the formula R 1 C(O)N(R 2 )CH 2 (CHOH) n CH 2 OH, wherein R 1 is a C 1 -C 3 alkyl, R 2 is C 10 -C 22 alkyl, and n is 3 or 4.
  • the N-acylpolyhydroxyalkyl-amine is added as a soil suspending agent.
  • U.S. Patent 3,654,166, Issued April 4, 1972, to H. W. Eckert, et al. relates to detergent compositions comprising at least one surfactant selected from the group of anionic, zwitterionic, and nonionic surfactants and, as a textile softener, an N-acyl, N-alkyl polyhydroxylalkyl compound of the formula R 1 N(Z)C(O)R 2 wherein R 1 is a C 10 -C 22 alkyl, R 2 is a C 7 -C 21 alkyl, R 1 and R 2 total from 23 to 39 carbon atoms, and Z is a polyhydroxyalkyl which can be -CH 2 (CHOH) m CH 2 OH where m is 3 or 4.
  • U.S. Patent 4,021,539, Issued May 3, 1977, to H. Möller, et al. relates to skin treating cosmetic compositions containing N-polyhydroxylalkyl-amines which Include compounds of the formula R 1 N(R)CH(CHOH) m R 2 wherein R 1 is H, lower alkyl, hydroxy-lower alkyl, or aminoalkyl, as well as heterocyclic aminoalkyl, R is the SUM as R 1 but both cannot be H, and R 2 is CH 2 OH or COOH.
  • French Patent 1,360,018, April 26, 1963, assigned to Commercial Solvents Corporation, relates to solutions of formaldehyde stabilized against polymerization with the addition of amides of the formula RC(O)N(R 1 )G wherein R is a carboxylic acid functionality having at least seven carbon atoms, R 1 is hydrogen or a lower alkyl group, and G is a glycitol radical with at least 5 carbon atoms.
  • G.B. Patent 745,036, published February 15, 1956, assigned to Atlas Powder Company, relates to heterocyclic amides an carboxylic esters thereof that are said to be useful as chemical intermediates, emulsifiers, wetting and dispersing agents detergents, textile softeners, etc.
  • the compounds are expressed by the formula N(R)(R 1 )C(O)R 2 wherein R is the residue of a anhydrized hexane pentol or a carboxylic acid ester thereof, R 1 is a monovalent hydrocarbon radical, and -C(O)R 2 is the acyl radical of a carboxylic acid having from 2 to 25 carbon atoms.
  • the detergent composition of the present invention comprise three essential components, viz. a polyhydroxy fatty acid amide, a water insoluble ethylene oxide adduct of a C 11 -C 15 aliphatic alcohol and a water soluble surfactant that may be anionic, cationic, ampholytic or zwitterionic.
  • the polyhydroxy fatty acid amide surfactant component of the present invention comprises compounds of the structural formula:
  • R 1 is H, C 1 -C 4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl, or a mixture thereof, preferably C 1 -C 4 alkyl, more preferably C 1 or C 2 alkyl, most preferably C 1 alkyl (i.e., methyl); and R 2 is a C 5 -C 31 hydrocarbyl, preferably straight chain
  • Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof.
  • Z preferably will be derived from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose.
  • high dextrose com syrup, high fructose corn syrup, and high maltose corn syrup can be utilized as well as the Individual sugars listed above. These corn syrups may yield a mix of sugar components for Z. It should be understood that it is by no means Intended to exclude other suitable raw materials.
  • Z preferably will be selected from the group) consisting of -CH 2 -(CHOH) n -CH 2 OH, -CH(CH 2 OH)-(CHOH) n-1 -CH 2 OH, -CH 2 -(CHOH) 2 (CHOR')(CHOH)-CH 2 OH, where n Is an integer from 3 to 5, inclusive, and R' is H or a cyclic or aliphatic monosaccharide, and alkoxylated derivatives thereof. Most preferred are glycityls wherein n is 4, particularly -CH 2 -(CHOH) 4 -CH 2 OH.
  • R 1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
  • R 2 -CO-N ⁇ can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
  • the most preferred polyhydroxy fatty acid amide has the general formula
  • R 2 is a C 11 -C 19 straight-chain alkyl or alkenyl group.
  • polyhydroxy fatty acid amides are known in the art. In general, they can be made by reacting an alkyl amine with a reducing sugar in a reductive amination reaction to form a corresponding N-alkyl polyhydroxyamine, and then reacting the N-alkyl polyhydroxyamine with a fatty aliphatic ester or triglyceride in a condensation/amidation step to form the N-alkyl, N-polyhydroxy fatty acid amide product.
  • Processes for making compositions containing polyhydroxy fatty acid amides are disclosed, for example, in G.B. Patent Specification 809,060, published February 18, 1959, by Thomas Hedley & Co., Ltd., U.S.
  • the amount of catalyst is preferably from about 0.5 mole % to about 50 mole %, more preferably from about 2.0 mole % to about 10 mole %, on an N-alkyl or N-hydroxyalkyl-glucamine molar basis.
  • the reaction is preferably carried out at from about 138oC to about 170oC for typically from about 20 to about 90 minutes.
  • the reaction is also preferably carried out using from about 1 to about 10 weight % of a phase transfer agent, calculated on a weight percent basis of total reaction mixture, selected from saturated fatty alcohol polyethoxylates, alkylpolyglycosides, linear glycamide surfactant, and mixtures thereof.
  • polyhydroxy fatty acid amide materials are sourced from tallow fat such that R. 2 is a C 15 -C 17 straight chain alkyl group.
  • compositions of the present invention are compositions of the present invention.
  • Such alcohol isoethyl alcohol
  • ethyoxylates should have an ethylene oxide content of less than 50% by weight and should be water insoluble.
  • a preferred aliphatic alcohol ethoxylate is a linear or
  • substantially linear aliphatic alcohol containing an average of 12-15 carbon atoms in the alkyl chain, ethoxylated with an average of three ethoxy groups per mole of alcohol.
  • the additional nonionic surfactant is present at a level of at least 1%, preferably from 1% to 10% and more preferably from 1% to 6% by weight of the composition.
  • the third essential component of laundry detergent is the third essential component of laundry detergent
  • compositions in accordance with the invention is one or more water soluble surfactants selected from anionic, cationic, ampholytic and zwitterionic surfactants.
  • the laundry detergent compositions of the present invention can contain, in addition to the nonionic surfactant system of the present invention, one or more anionic surfactants as described below.
  • Alkyl ester sulfonate surfactants hereof include linear esters of C 8 -C 20 carboxylic acids (i.e., fatty acids) which are sulfonated with gaseous SO 3 according to "The Journal of the American Oil Chemists Society," 52 (1975), pp. 323-329. Suitable starting materials would Include natural fatty substances as derived from tallow, palm oil, etc.
  • alkyl ester sulfonate surfactant especially for laundry applications, comprise alkyl ester sulfonate surfactants of the structural formula:
  • R 3 is a C 8 -C 20 hydrocarbyl, preferably an alkyl, or combination thereof
  • R 4 is a C 1 -C 6 hydrocarbyl, preferably an alkyl, or combination thereof
  • H is a cation which forms a water soluble salt with the alkyl ester sulfonate.
  • Suitable salt-forming cations include metals such as sodium, potassium, and lithrum, and substituted or unsubstituted ammonium cations, such as monoethanolamine, diethanolamine, and triethanolamine.
  • R 3 is C 10 -C 16 alkyl
  • R 4 is methyl, ethyl or isopropyl.
  • the methyl ester sulfonates wherein R 3 iS C 10 -C 16 alkyl.
  • Alkyl sulfate surfactants hereof are water soluble salts or acids of the formula ROSO 3 M wherein R preferably is a C 10 -C 24 hydrocarbyl, preferably an alkyl or hydroxyalkyl having a C 10 -C 20 alkyl component, more preferably a C 12 -C 18 alkyl or hydroxyalkyl, and M is H or a cation, e.g., an alkali metal cation (e.g., sodium, potassium, lithium), or ammonium or substituted ammonium (e.g., methyl-, dimethyl-, and trimethyl ammonium) cations and quaternary ammonium cations such as tetramethyl -ammonium and dimethyl piperdinium cations and quaternary ammonium cations derived from al kylamines such as ethyl amine, di ethylamine, triethyl amine, and mixtures thereof, and the l
  • Al kyl alkoxylated sulfate surfactants hereof are water sol uble salts or adds of the formula RO(A) m SO 3 M wherein R is an unsubstituted C 10 -C 24 alkyl or hydroxyal kyl group having a C 10 -C 24 alkyl component, preferably a C 12 -C 20 alkyl or hydroxyalkyl , more preferably an alkyl group having from 12 to 18 carbon atoms, especially from 12 to 15 carbon atoms.
  • A is an ethoxy or propoxy unit
  • m is greater than zero, typically between about 0.5 and about 6, more preferably between about 0.5 and about 3
  • M is H or a cation which can be, for example, a metal cation (e.g., sodium, potassium, lithium, calcium, magnesium, etc.), ammonium or substituted-ammonium cation.
  • a metal cation e.g., sodium, potassium, lithium, calcium, magnesium, etc.
  • Alkyl ethoxylated sulfates as well as alkyl propoxylated sulfates are contemplated herein.
  • substituted ammonium cations include methyl-, dimethyl-, trimethyl-ammonium cations and quaternary ammonium cations such as tetramethyl-ammonium and dimethyl piperdinium cations and those derived from alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof, and the like.
  • alkyl alkoxylated sulfate surfactants are the C 12 -C 18 alkyl ethoxy sulfates containing an average ofup to three ethoxy groups per mole of alkyl ethoxy sulfate.
  • a particularly preferred surfactant is C 12 -C 15 alkyl
  • Other exemplary surfactants include C 12 -C 18 alkyl polyethoxylate (1.0) sulfate (C 12 -C 18 E(1.0)M), C 12 -C 18 alkyl polyethoxylate (2.25) sulfate (C 12 -C 18 E(2.25)M), C 12 -C 18 alkyl polyethoxylate (3.0) sulfate (C 12 -C 18 E(3.0)M), and C 12 -C 18 alkyl polyethoxylate (4.0) sulfate (C 12 -C 18 E(4.0)M), wherein M is conveniently selected from sodium and potassium.
  • anionic surfactants useful for detersive purposes can also be included in the laundry detergent compositions of the present invention.
  • These can include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of soap, C 9 -C 20 linear alkylbenzenesulfonates, C 8 -C 22 primary or secondary alkanesulfonates, C 8 -C 24 olefinsulfonates, sulfonated polycarboxylic acids prepared by sulfonation of the pyrolyzed product of alkaline earth metal citrates, e.g., as described in British patent specification No.
  • alkylpolyglycolethersvlfates (containing up to. 10 moles of ethylene oxide); alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleyl glycerol sulfates, alkyl phenol ethylene oxide ether sulfates, paraffin sulfonates, alkyl phosphates, isethionates such as the acyl isethionates, N-acyl taurates, alkyl succinamates and sulfosuccinates, monoesters of sulfosuccinates (especially saturated and unsaturated C 12 -C 18 monoesters) and diesters of sulfosuccinates (especially saturated and unsaturated C 5 -C 12 diesters), acyl sarcosinates, sulfates of alkylpolysacchar-ides such as the
  • Resin acids and hydrogenated resin acids are also suitable, such as rosin, hydrogenated rosin, and resin acids and hydrogenated resin acids present in or derived from tall oil. Further examples are described in "Surface Active Agents and Detergents" (Vol. I and II by Schwartz, Perry and Berch). A variety of such surfactants are also generally disclosed in U.S. Patent 3,929,678, issued December 30, 1975 to Laughlin, et al. at Column 23, l ine 58 through Column 29, line 23 (herein incorporated by reference).
  • detergent compositions of the invention are free of alkyl benzene sulfonate salts.
  • a highly preferred system comprises a mixture of a major proportion of a water-soluble C 14 -C 15 alkyl sulfate and a minor proportion of a C 12 -C 15 alkyl ethoxysulfate containing an average of three ethoxy groups per mole of alkyl ethoxy sulfate.
  • the laundry detergent compositions of the present invention typically comprise from about 1% to about 20%, preferably from about 3% to about 15% and most preferably from 5% to 10% by weight of anionic surfactants.
  • the laundry detergent compositions of the present invention may also contain cationic, ampholytic, zwitterionic, and semi-polar surfactants
  • Cationic detersive surfactants suitable for use in the laundry detergent compositions of the present invention are those having one 0000-chain hydrocarbyl group.
  • cationic surfactants include the ammonium surfactants such as alkyl dimethyl ammonium halogenides, and those surfactants having the formula:
  • R 2 Is an alkyl or alkyl benzyl group having from about 8 to about 18 carbon atoas In the alkyl chain, each R 3 is selected from, the group consisting of -CH 2 CH 2 -, -CH 2 CH(CH 3 )-, -CH 2 CH(CH 2 OH)-, -CH 2 CH 2 CH 2 -, and mixtures thereof; each R 4 Is selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 hydroxy-alkyl, benzyl ring structures formed by joining the two R 4 groups, -CH 2 CHOH-CHOHCOR 6 CHOHCH 2 OH wherein R 6 is any hexose or hexose polymer having a molecular weight less: than about 1000, and hydrogen when y is not O; R 5 .
  • R 4 is the same as R 4 or is an alkyl chain wherein the total number of carbon atoms of R 2 plus R 5 is not more than about 18; each y Is frost 0 to about 10 and the sum of the y values is from 0 to about 15; and X is any compatible anion.
  • Other cationic surfactants useful herein are also described in U.S. Patent 4,228,044, Cambre, issued October 14, 1980, incorporated herein by reference.
  • the laundry detergent compositions of the present invention typically comprise from 0% to about 25%, preferably from about 3% to about 15% by weight of such cationic surfactants.
  • Ampholytic surfactants are also suitable for use in the laundry detergent compositions of the present invention. These surfactants can be broadly described as aliphatic derivatives of secondary or tertiary amines, or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic radical can be straight- or branched-chain.
  • One of the aliphatic substituents contains at least about 8 carbon atoms, typically from about 8 to about 18 carbon atoms, and at least one contains an anionic water-solubilizing group, e.g., carboxy, sulfonate, sulfate. See U.S. Patent No.3,929,678 to Laughlin et al., issued December 30, 1975 at column 19, lines 18-35 (herein incorporated by reference) for examples of ampholytic surfactants.
  • the laundry detergent compositions of the present Invention typically comprise from 0% to about 15%, preferably from about 1% to about 10% by weight of such ampholytic surfactants.
  • Zwitterionic surfactants are also suitable for use in laundry detergent compositions. These surfactants can be broadly described as derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds. See U.S. Patent No. 3,929,678 to Laughlin et al., issued December 30, 1975 at column 19, line 38 through column 22, line 48 (herein incorporated by reference) for examples of zwitterionic surfactants.
  • Semi-polar nonionic detergent surfactants include the amine oxide surfactants having the formula
  • amine oxide surfactants in particular include C 10 -C 18 alkyl dimethyl amine oxides and C 8 -C 12 alkoxy ethyl dihydroxy ethyl amine oxides.
  • the level of builder can vary widely depending upon the end use of the composition and Its desired physical form.
  • Liquid formulations typically comprise at least about 1%, more typically from about 5% to about 50%, preferably about 5% to about 30%, by weight of detergent builder.
  • Granular formulations typically comprise at least about 1%, more typically from about 10% to about 80%, preferably from about 15% to about 50% by weight of the detergent builder.
  • Lower or higher levels of builder, however, are not meant to be excluded.
  • Inorganic detergent builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates (exemplified by the tripolyphosphates, pyrophosphates, and glassy polymeric meta-phosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulfates, and aluminosilicates.
  • Borate builders, as well as builders containing borate-forming materials that can produce borate under detergent storage or wash conditions canalso be used but are not preferred at wash conditions less than about 50°C, especially less than about 40°C.
  • Preferred builder systems are also free of phosphatee.
  • silicate builders are the alkali metal silicates, particularly those having a SiO 2 :Na 2 O ratio in the range 1.6:1 to 3.2:1 and layered silicates, such as the layered sodium silicates.
  • Preferred crystalline layered sodium silicates have the general formula wherein M is sodium or hydrogen, x is a number from 1.9 to 4 and y is a number from 0 to 20. Crystalline layered sodium silicates of this type are disclosed in EP-A-0164514 and methods for their preparation are disclosed in DE-A-3417649 and DE-A-3742043, incorporated herein by reference.
  • x in the general formula above has a value of 2, 3 or 4 and is preferably 2.
  • M is sodium and y is O and preferred examples of this formula comprise the ⁇ -, ⁇ - ⁇ - and ⁇ - forms of Na 2 Si 2 O 5 .
  • These materials are available from Hoechst AG FRG as respectively NaSKS-5, NaSKS-7, NaSKS-11 and NaSKS-6.
  • the most preferred material is ⁇ -Na 2 Si 2 O 5 , NaSKS-6.
  • silicates may also be useful such as for example magnesium silicate, which can serve as a crispening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
  • magnesium silicate which can serve as a crispening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
  • carbonate builders are the alkaline earth and alkali metal carbonates, including sodium carbonate and sesqui-
  • Aluminosilicate builders are especially useful in the present invention. Aluminosilicate builders are of great importance most currently marketed heavy duty granular detergent compositions, and can also be a significant builder ingredient in liquid detergent formulations. Aluminosilicate builders include those having the empirical formula:
  • M is sodium, potassium, ammonium or substituted ammonium
  • z is from about 0.5 to about 2; and y is 1; this material having a magnesium ion exchange capacity of at least about 50 milligram equivalents of CaCO 3 hardness per gram of anhydrous aluminosilicate.
  • Preferred aluminosilicates are zeolite builders which have the formula:
  • z and y are integers of at least 6, the molar ratio of z to y is in the range from 1.0 to about 0.5, and x is an integer from about 15 to about 264.
  • aluminosilicate ion exchange materials are commercially available. These aluminosilicates can be crystalline or amorphous in structure and can be naturally-occurring aluminosilicates or synthetically derived. A method for producing aluminosilicate ion exchange materials is disclosed in U.S. Patent 3,985,669, Krummel, et al., issued October 12, 1976, incorporated herein by reference. Preferred synthetic crystalline aluminosilicate ion exchange materials useful herein are available under the designations Zeolite A, Zeolite P (B), and Zeolite X. In a especially preferred embodiment, the crystalline aluminosilicate ion exchange material has the formula:
  • x is from about 20 to about 30, especially about 27.
  • This material is known as Zeolite A.
  • the aluminosilicate has a particle size of about 0.1-10 microns in diameter.
  • Specific examples of polyphosphates are the alkali metal tripolyphosphates, sodium, potassium and ammonium pyrophosphate, sodium and potassium and ammonium pyrophosphate, sodium and potassium orthophosphate, sodium polymeta phosphate in which the degree of polymerization ranges from about 6 to about 21, and salts of phytic acid.
  • phosphonate builder salts are the water-soluble salts of ethane 1-hydroxy-l,l-diphosphonate particularly the sodium and potassium salts, the water-soluble salts of methylene diphosphonic acid e.g. the trisodium and tripotassium salts and the water-soluble salts of substituted methylene diphosphonic acids, such as the trisodium and tripotassium ethylidene, isopyropylidene benzylmethylidene and halo methylidene phosphonates.
  • Phosphonate builder salts of the aforementioned types are disclosed in U.S. Patent Nos.
  • Polycarboxylate builder can generally be added to the composition in acid form, but can also be added in the form of a neutralized salt.
  • al kal i metal s such as sodium, potassium, and lithium salts, especially sodium salts, or ammonium and substituted ammonium (e.g., alkanolammonium) salts are preferred.
  • polycarboxylate builders include a variety of categories of useful materials.
  • One important category of polycarboxylate builders encompasses the ether polycarboxylates.
  • a number of ether polycarboxylates have been disclosed for use as detergent builders.
  • Examples of useful ether polycarboxylates include oxydisuccinate, as disclosed in Berg, U.S. Patent 3,128,287, Issued April 7, 1964, and Lamberti et al., U.S. Patent 3,635,830, Issued January 18, 1972, both of which are incorporated herein by reference.
  • a specific type of ether polycarboxylates useful as builders in the present invention also include those having the general formula:
  • A is H or OH; B is H or -O-CH(COOX)-CH 2 (COOX); and X is H or a salt-forming cation.
  • a and B are both H, then the compound is oxydissuccinic acid and its water-soluble salts. If A is OH and B is H, then the compound is tartrate monosuccinic acid (TMS) and its water-soluble salts. If A is H and B is -O-CH(COOX)-CH 2 (COOX), then the compound is tartrate disuccinic acid (TDS) and its water-soluble salts. Mixtures of these builders are especially preferred for use herein.
  • mixtures of TMS and TDS in a weight ratio of TMS to TDS of from about 97:3 to about 20:80 are disclosed in U.S. Patent 4,663,071, issued to Bush et al., on May 5, 1987.
  • Suitable ether polycarboxylates also include cyclic compounds, particularly alicyclic compounds, such as those described in U.S. Patents 3,923,679; 3,835,163; 4,158,635; 4,120,874 and 4,102,903, all of which are incorporated herein by reference.
  • ether hydroxypolycarboxylates represented by the structure:
  • n is from about 2 to about 15 (preferably n is from about 2 to about 10, more preferably n averages from about 2 to about 4) and each R is the same or different and selected from hydrogen, C 1-4 alkyl or C 1-4 substituted alkyl (preferably R is hydrogen).
  • Still other ether polycarboxylates include copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene-2, 4, 6-trisulfonic acid, and carboxymethyl-oxysuccinic acid.
  • Organic polycarboxylate builders also include the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids. Examples of polyacetic acid builder salts are the sodium, potassium, lithium, ammonium and substituted ammonium salts of ethylenediamine tetraacetic acid and nitrilotriacetic acid.
  • Amino carboxylates useful as optional chelating agents in compositions of the invention can have one or more, preferably at least two, units of the substructure ,
  • the water-soluble ethoxylated amines are preferably selected from the group consisting of:
  • polycarboxylate materials which can be employed as the polymeric polycarboxylate dispersing agent are these polymers or copolymers which contain at least about 60% by weight of segments with the general formula
  • Polymeric polycarboxylate materials of this type can be prepared by polymerizing or copolymerizing suitable unsaturated monomers, preferably in their acid form.
  • Unsaturated monomeric acids that can be polymerized to form suitable polymeric polycarboxylates include acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid and methylenemalon1c acid.
  • the presence in the polymeric polycarboxylates herein of monomeric segments, containing no carboxylate radicals such as vinylmethyl ether, styrene, ethylene, etc. is suitable provided that such segments do not constitute more than about 40% by weight.
  • Soluble acrylate/maleate copolymers of this type are known materials which are described in European Patent Application No. 66915, published December 15, 1982, which publication is Incorporated herein by reference. If utilized, the polymeric dispersing agents will generally comprise from about 0.2% to about 10%, preferably from about 1% to about 5% by weight of the laundry detergent compositions.
  • Optical brighteners or other brightening or whitening agents known to those skilled in the art can be incorporated into the laundry detergent compositions of the present invention.
  • the choice of brightener will depend upon a number of factors, such as the type of detergent, the nature of other components present in the detergent composition, the temperatures of wash water, the degree of agitation, and the ratio of the material washed to tub size.
  • Stilbene derivatives include, but are not necessarily limited to, derivatives of bis(triazinyl)amino-stilbene; bisacylamino derivatives of stilbene; triazole derivatives of stilbene; oxadlazole derivatives of stilbene; oxazole derivatives of stilbene; and styryl derivatives of stilbene.
  • Certain derivatives of bis(triazinyl)aminostilbene may be prepared from 4,4'-diamine-stilbene-2,2'-disulfonic acid.
  • Coumarin derivatives include, but are not necessarily limited to, derivatives substituted in the 3-position, in the 7-position, and in the 3- and 7-positions.
  • the styrylazoles can be further subclassified into styrylbenzoxazoles, styryl imidazoles and styrylthiazoles, as disclosed on page 78 of the Zahradnik reference. It will be understood that these three identified subclasses may not necessarily reflect an exhaustive list of subgroups into which styrylazoles may be subclassified.
  • miscellaneous agents may also be useful as brighteners.
  • miscellaneous agents are disclosed at pages 93-95 of the Zahradnik reference, and include 1-hydroxy-3,6,8-pyrenetrisulfonic acid; 2,4-dimethoxy-1,3,5-triazin-6-yl-pyrene; 4,5-diphenylimidazolonedisulfonic acid; and derivatives of pyrazolinequinoline.
  • Tinopal UNPA Tinopal CBS and Tinopal 5BM
  • Ciba-Geigy available from Ciba-Geigy
  • Arctic White CC available from Hilton-Davis, located in Italy
  • 2-(4-styrylphenyl)-2H-naphthol[1,2-d]triazoles 4,4'-bis-(1,2,3-triazol-2- yl)-stilbenes
  • 4,4'-bis(styryl)bisphenyls 4,4'-bis(styryl)bisphenyls
  • the y-amino- coumarins include: Tinopal UNPA, Tinopal CBS and Tinopal 5BM; available from Ciba-Geigy; Arctic White CC and Artie White CWD, available from Hilton-Davis, located in Italy
  • the 2-(4-styrylphenyl)-2H-naphthol[1,2-d]triazoles 4,4'-bis-(1,2,3-tri
  • the optical brighteners will generally comprise from about 0.05% to about 2.0%, preferably from about 0.1% to about 1.0% by weight of the laundry detergent compositions.
  • suds suppressors are well known to those skilled in the art. They are generally described, for example, in Kirk Othmer Encyclopedia of Chemical Technology, Third Edition, Volume 7, pages 430-447 (John Wiley & Sons, Inc., 1979).
  • One category of suds suppressor of particular interest encompasses monocarboxylic fatty acids and soluble salts thereof. These materials are discussed in U.S. Patent 2,954,347, issued September 27, 1960 to Wayne St. John, said patent being Incorporated herein by reference.
  • the monocarboxylic fatty acids, and salts thereof, for use as suds suppressor typically have hydrocarbyl chains of 10 to about 24 carbon atoms, preferably 12 to 18 carbon atoms.
  • Suitable salts include the alkali metal salts such as sodium, potassium, and lithium salts, and ammonium and alkanolammonium salts. These materials are a preferred category of suds suppressor for detergent compositions.
  • the laundry detergent compositions of the present invention may also contain non-surfactant suds suppressors.
  • non-surfactant suds suppressors include, for example, high molecular weight hydrocarbons such as paraffin, fatty acid esters (e.g., fatty acid triglycerldes), fatty acid esters of monovalent alcohols, aliphatic C 18 -C 40 ketones (e.g. stearone), etc.
  • suds inhibitors include N-alkylated amino trlazlnes such as tri- to hexa-alkylmelamines or di- to tetra-alkyldiamine chlortriazines formed as products of cyanuric chloride with two or three moles of a primary or secondary amine containing 1 to 24 carbon atoms, propylene oxide, and monostearyl phosphates such as monostearyl alcohol phosphate ester and monostearyl di-alkali metal (e.g., sodium, potassium, lithium) phosphates and phosphate esters.
  • the hydrocarbons, such as paraffin and haloparaffin can be utilized in liquid form.
  • the liquid hydrocarbons will be liquid at room temperature and atmospheric pressure, and will have a pour point in the range of about -40oC and about 5oC, and a minimum boiling point not less than about 110oC (atmospheric pressure). It is also known to utilize waxy hydrocarbons, preferably having a melting point below about 100oC.
  • the hydrocarbons constitute a preferred category of suds suppressor for detergent compositions. Hydrocarbon suds suppressors are described, for example, in U.S. Patent 4,265,779, issued May 5, 1981 to Gandolfo, et al., incorporated herein by reference.
  • the hydrocarbons thus, include aliphatic, alicyclic, aromatic, and heterocycllc saturated or unsaturated hydrocarbons having from about 12 to about 70 carbon atoms.
  • the term "paraffin,” as used, in this suds suppressor discussion, is intended to include mixtures of true paraffins and cyclic hydrocarbons.
  • Non-surfactant suds comprises silicone suds suppressors.
  • This category includes the use of polyorganosiloxane oils, such as polydimethylsiloxane, dispersions or emulsions of polyorganosiloxane oils or resins, and combinations of polyorganosiloxane with silica particles wherein the polyorganosiloxane is chemisorbed of fused onto the silica.
  • silicone suds suppressors are well known in the art and are, for example, disclosed in U.S. Patent 4,265,779, issued May 5, 1981 to
  • 3,455,839 which relates to compositions and processes for defoaming aqueous solutions by incorporating therein small amounts of polydimethylsiloxane fluids.
  • silicone and silanated silica are described, for instance, in German Patent Application DOS 2,124,526.
  • Silicone defoamers and suds controlling agents in granular detergent compositions are disclosed in U.S. Patent 3,933,672, Bartolotta et al., and in U.S. Patent 4,652,392, Baginski et al., issued March 24, 1987.
  • An exemplary silicone based suds suppressor for use herein is a suds suppressing amount of a suds controlling agent consisting essentially of:
  • polydimethylsiloxane fluid having a viscosity of from about 20 cs. to about 1500 cs. at 25oC;
  • siloxane resin composed of (CH 3 ) 3 SiO 1/2 units of SiO 2 units in a ratio of from (CH 3 ) 3 SiO 1/2 units and to SiO 2 units of from about 0.6:1 to about 1.2:1; and (111) from about 1 to about 20 parts per 100 parts by weight of
  • Suds suppressors when utilized, are present in a “suds suppressing amount.”
  • Suds suppressing amount is meant that the formulator of the composition can select an amount of this suds controlling agent that will control the suds to the extent desired.
  • the amount of suds control will vary with the detergent surfactant selected. For example, with high sudsing surfactants, relatively more of the suds controlling agent is used to achieve the desired suds control than with low foaming surfactants.
  • the laundry detergent compositions of the present invention will generally comprise from 0% to about 5% of suds suppressor.
  • monocarboxylic fatty acids, and salts, thereof When utilized as suds suppressors, monocarboxylic fatty acids, and salts, thereof, will be present typically in amounts up to about 5%, by weight, of the detergent composition.
  • from about 0.5% to about 3% of fatty monocarboxylate suds suppressor is utilized.
  • Silicone suds suppressors are typically utilized in amounts up to about 2.0%, by weight, of the detergent composition, although higher amounts may be used. This upper limit is practical in nature, due primarily to concern with keeping costs minimized and effectiveness of lower amounts for effectively controlling sudsing.
  • from about 0.01% to about 1% of silicone suds suppressor is used, more preferably from about 0.255.
  • these weight percentage values include any silica that may be utilized in combination with polyorganosiloxane, as well as any adjunct materials that may be utilized.
  • Monostearyl phosphates are generally utilized in amounts ranging from about 0.1% to about 2% by weight of the compositions.
  • Hydrocarbon suds suppressors are typically utilized in amounts ranging from about 0.01% to about 5.0%, although higher levels can be used.
  • laundry detergent compositions of the present invention include other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations, etc.
  • Liquid detergent compositions can contain water and other solvents as carriers.
  • Low molecular weight primary or secondary alcohols exemplified by methanol, ethanol, propanol, and isopropanol are suitable.
  • Monohydric alcohols are preferred for solubilizing surfactant, but polyols such as those containing from about 2 to about 6 carbon atoms and from about 2 to about 6 hydroxy groups (e.g., propylene glycol, ethylene glycol, glycerine, and 1,3-propanediol) can also be used.
  • the laundry detergent compositions of the present invention will preferably be formulated such that during use in aqueous cleaning operations, the wash water will have a pH of between about 6.5 and about 11, preferably between about 7.5 and about 10.5.
  • Liquid product formulations preferably have a pH between about 7.5 and about 9.5, more preferably between about 7.5 and about 9.0.
  • Techniques for controlling pH at recommended usage levels include the use of buffers, alkali, acids, etc., and are well known to those skilled in the art.
  • This invention further provides a method for cleaning substrates, such as fibers, fabrics, hard surfaces, skin, etc., by contacting said substrate with a detergent composition containing the nonionic surfactant system of the present invention, wherein the weight ratio of polyhydroxy fatty acid amide to additional surfactant in the nonionic surfactant system is in the range of from about 1:5 to about 5:1, in the presence of a solvent such as water or a water-miscible solvent (e.g., primary and secondary alcohols).
  • a solvent such as water or a water-miscible solvent (e.g., primary and secondary alcohols).
  • Agitation is preferably provided for enhancing cleaning.
  • Suitable means for providing agitation include rubbing by hand preferably with the aid of a brush, or other cleaning device, automatic laundry washing machines, automatic dishwashers, etc.
  • one suitable apparatus for use herein comprises a three-liter four-necked flask fitted with a motor-driven paddle stirrer and a thermometer of length sufficient to contact the reaction medium.
  • the other two necks of the flask are fitted with a nitrogen sweep and a wide-bore side-arm (caution: a wide-bore side-arm is important in case of very rapid methanol evolution) to which is connected an efficient collecting condenser and vacuum outlet.
  • the latter is connected to a nitrogen bleed and vacuum gauge, then to an aspirator and a trap.
  • a 500 watt heating mantle with a variable transformer temperature controller (“Variac”) used to heat the reaction is so placed on a lab-jack that it may be readily raised or lowered to further control temperature of the reaction.
  • Variac variable transformer temperature controller
  • N-methylglucamine (195 g., 1.0 mole, Aldrich, M4700-0) and methyl laurate (Procter & Gamble CE 1270, 220.9 g., 1.0 mole) are placed in a flask.
  • the solid/liquid mixture is heated with stirring under a nitrogen sweep to form a melt (approximately 25 minutes).
  • catalyst anhydrous powdered sodium carbonate, 10.5 g., 0.1 mole, J. T. Baker
  • the nitrogen sweep is shut off and the aspirator and nitrogen bleed are adjusted to give 5 inches (5/31 atm.) Hg. vacuum. From this point on, the reaction temperature is held at 150o C by adjusting the Variac and/or by raising or lowering the mantle.
  • TGA Glucityl tallow fatty acid amide
  • TAS Sodium tallow alcohol sulfate
  • TAE n Tallow alcohol ethoxylated with n moles of ethylene oxide per mole of alcohol.
  • CMC Sodium carboxymethyl cellulose
  • Zeolite A Hydrated Sodium Aluminosilicate of formula Na 12 (A1O 2 SiO 2 ) 12 .27H 2 O having a primary particle size in the range from 1 to 10 micrometers
  • Enzyme Mixed proteolytic and amyloytic enzyme sold by Novo Industries AS.
  • AEG Lavamat 980 automatic washing machines were used to carry out a similar comparison of the products.
  • Six replicates for each product were carried out.
  • Each wash load comprised 3kg of realistically soiled ballast fabrics composed of cotton sheets and towels together with polycotton items to give a cotton:polycotton weight ratio of approximately 3:1, together with sets of stained swatches.
  • the stain sets comprised:
  • each swatch was dried and then assessed by an expert panel using a five point Scheffé scale.
  • the results of both test techniques are set out below.
  • the LH column shows the advantage for Composition A over Composition B while the RH column shows the advantage for
  • Composition A over Composition C.
  • compositions A&B provides stain removal benefits relative to Composition C over a wide spectrum of soil types and fabrics.
  • the comparison of compositions A&B shows the surprising benefit provided by the use of a combination in accordance with the invention relative to that provided by use of a higher level of the polyhydroxy fatty acid amide alone.
  • Composition A of Example I was compared to a commercially available detergent composition (D) which differed from
  • Composition A only in that the 45AS, 25AE3S, TGA and 25E3 components were replaced by 7.6% C 12 LAS, 3% 45E7 and 1.1% TAE 11
  • the comparison was carried out in AEG Lavamat 980 washing machines using the wash conditions and procedure of Example 1 and a variety of stains on cotton, polycotton and polyester fabric swatches. Assessment of the washed fabric swatches by an expert panel using a five point Scheffé scale showed that
  • Composition A provided a stain removal benefit over Composition D of
  • Composition A of Example I was compared to that of two further detergent Compositions D and E which differed from A only in that the 25E3 component was replaced by 68E3 and 68E5 respectively, where 68E3 and 68E5 are C 16 -C 18 predominantly linear primary alcohols condensed with an average of three and five moles of ethylene oxide respectively.
  • the performance comparisons were made using the conditions and procedure of the tergotometer test of Example I.
  • composition A in accordance with the invention, provided significant stain removal benefits over both compositions D and E, neither of which is a composition in accord with the invention.

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  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cleaning Implements For Floors, Carpets, Furniture, Walls, And The Like (AREA)
PCT/US1992/004902 1991-06-18 1992-06-11 Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol WO1992022629A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP5501005A JPH06508394A (ja) 1991-06-18 1992-06-11 ポリヒドロキシ脂肪酸アミドと不溶性エトキシ化アルコールとを含有する洗濯洗剤
AU22482/92A AU667047B2 (en) 1991-06-18 1992-06-11 Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol
DE69222418T DE69222418T2 (de) 1991-06-18 1992-06-11 Waschmittel enthaltend Polyhydroxyfettsäureamide und unlöslichen ethoxylierten Alkohol
BR9206176A BR9206176A (pt) 1991-06-18 1992-06-11 Composições de limpeza de tecido e mais particularmente a composições de limpeza de tecido capazes de provimento de remoção de mancha de graxa e oleosa
EP92914366A EP0591397B1 (en) 1991-06-18 1992-06-11 Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol
GR970402296T GR3024776T3 (en) 1991-06-18 1997-09-25 Laundry detergent containing a polyhydroxy fatty amide and insoluble ethoxylated alcohol

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GB919113139A GB9113139D0 (en) 1991-06-18 1991-06-18 Detergent compositions
GB9113139.1 1991-06-18

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5354510A (en) * 1992-07-02 1994-10-11 L'oreal Use in surface-active agent solutions of aminopolyol carbamates as thickening agents and compositions containing them
WO1995002666A1 (de) * 1993-07-12 1995-01-26 Henkel Kommanditgesellschaft Auf Aktien Klarspülmittel für die maschinelle reinigung harter oberflächen
EP0709450A1 (en) * 1994-10-24 1996-05-01 The Procter & Gamble Company Low sudsing liquid detergent compositions
WO1997002335A1 (de) * 1995-07-04 1997-01-23 Henkel Kommanditgesellschaft Auf Aktien Niotensidkonzentrate
WO1999025796A3 (en) * 1997-11-18 1999-07-29 Unilever Plc Detergent powder compositions with glucamide-like bleach enhancers
US20220041957A1 (en) * 2018-12-21 2022-02-10 Clariant International Ltd. Glucamide-based surfactants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112023002786A2 (pt) * 2020-08-26 2023-03-14 Unilever Ip Holdings B V Composição detergente sólida para lavagem de roupas, método de lavagem de uma superfície têxtil com a composição detergente e uso

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US3868336A (en) * 1971-03-11 1975-02-25 Lever Brothers Ltd Process for improving flowability of detergents
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US4072621A (en) * 1974-11-13 1978-02-07 The Procter & Gamble Company Detergent composition
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US2965576A (en) * 1956-05-14 1960-12-20 Procter & Gamble Detergent compositions
US3654166A (en) * 1967-08-14 1972-04-04 Henkel & Cie Gmbh Detergent compositions
US3868336A (en) * 1971-03-11 1975-02-25 Lever Brothers Ltd Process for improving flowability of detergents
US3925224A (en) * 1973-04-17 1975-12-09 Church & Dwight Co Inc Detergent additive composition
US4072621A (en) * 1974-11-13 1978-02-07 The Procter & Gamble Company Detergent composition
US4110262A (en) * 1976-03-08 1978-08-29 The Procter & Gamble Company Liquid detergent composition

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5354510A (en) * 1992-07-02 1994-10-11 L'oreal Use in surface-active agent solutions of aminopolyol carbamates as thickening agents and compositions containing them
WO1995002666A1 (de) * 1993-07-12 1995-01-26 Henkel Kommanditgesellschaft Auf Aktien Klarspülmittel für die maschinelle reinigung harter oberflächen
US5691300A (en) * 1993-07-12 1997-11-25 Henkel Kommanditgesellschaft Auf Aktien Rinse aids for the machine washing of hard surfaces
EP0709450A1 (en) * 1994-10-24 1996-05-01 The Procter & Gamble Company Low sudsing liquid detergent compositions
WO1997002335A1 (de) * 1995-07-04 1997-01-23 Henkel Kommanditgesellschaft Auf Aktien Niotensidkonzentrate
WO1999025796A3 (en) * 1997-11-18 1999-07-29 Unilever Plc Detergent powder compositions with glucamide-like bleach enhancers
US20220041957A1 (en) * 2018-12-21 2022-02-10 Clariant International Ltd. Glucamide-based surfactants

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TR27927A (tr) 1995-10-16
CN1069763A (zh) 1993-03-10
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BR9206176A (pt) 1994-12-27
CA2111592A1 (en) 1992-12-23
GR3024776T3 (en) 1997-12-31
ES2106877T3 (es) 1997-11-16
IE921961A1 (en) 1992-12-30
ATE158612T1 (de) 1997-10-15
JPH06508394A (ja) 1994-09-22
EP0591397A1 (en) 1994-04-13
GB9113139D0 (en) 1991-08-07
EP0591397A4 (en) 1995-10-04
HUT66843A (en) 1995-01-30
AU2248292A (en) 1993-01-12
TW222308B (enrdf_load_stackoverflow) 1994-04-11
HU9303643D0 (en) 1994-04-28
HU213363B (en) 1997-05-28
CN1034083C (zh) 1997-02-19
DE69222418D1 (de) 1997-10-30
DE69222418T2 (de) 1998-04-16
MX9202991A (es) 1993-02-01
NZ243178A (en) 1995-06-27
AU667047B2 (en) 1996-03-07

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